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An equimolar mixture of two enantiomers, which is optically inactive due to the cancelling effect of the two enantiomers' rotations.

The spatial arrangement of groups around a chiral center relative to another chiral center, not necessarily specifying the exact 3D position.

A form of chirality that arises when a double bond or cyclic structure has different substituents, leading to geometric isomerism, that can be similar to chirality at tetrahedral centers.

The precise 3D spatial arrangement of the atoms around a chirality center, described by R and S nomenclature.

A set of rules used to define the absolute configuration of a chiral center, assigning R (rectus, right) or S (sinister, left) based on the priorities of substituents.

A compound with multiple stereocenters that possesses an internal plane of symmetry, making it achiral despite having chiral centers.

Molecules that are superimposable on their mirror images, lacking chirality.

Objects, including molecules, which are not superimposable on their mirror image, often possessing a center of asymmetry.

Isomers that have the same molecular formula and sequence of bonded atoms, but differ in the three-dimensional orientations of their atoms in space.

A type of diastereomerism where molecules have the same covalent bonds but differ in spatial orientation across a double bond or a ring structure.

A carbon atom bearing four distinct substituents, serving as the source of chirality in a molecule.

Stereoisomers resulting from restricted rotation around a bond, typically due to steric hindrance, and which can have different physical and chemical properties.

Stereoisomers that can be interconverted exclusively by rotation about formally single bonds.

Diastereomers that differ in configuration at only one chiral center out of several.

Epimers that result from the ring formation in carbohydrates, differing at the anomeric carbon.

A two-dimensional representation of a molecule that depicts stereochemistry, using horizontal lines for bonds coming out of the plane and vertical lines for bonds going into the plane.

Stereoisomers that are non-superimposable mirror images of each other.

The process of separating racemic mixtures into individual enantiomers.

Stereoisomers that are not mirror images of each other and are not superimposable.